Agents for Combating Plant Pests

ABSTRACT

The present invention relates to compositions for controlling plant pests, which contain the compound of the formula (I) 
     
       
         
         
             
             
         
       
     
     in a mixture with fungicidally active compounds, except for cyclopropylcarboxamide derivatives and azolylmethylcycloalkanes.

The present invention relates to pesticides which comprise an activecompound combination of the compound of the formula (I)

with fungicides.

Fungicidally active compounds, such as azole derivatives, aryl benzylethers, benzamide, morpholine compounds and other heterocycles, areknown (cf. K. H. Büchel “Pflanzenschutz and Schädlingsbekämpfung”, pages140 to 153, Georg Thieme-Verlag, Stuttgart 1977, EP publishedspecification 0 040 345, German Offenlegungsschrift 2 324 010, GermanOffenlegungsschrift 2 201 063, EP published specification 0 112 284, EPpublished specification 0 304 758 and DD patent specification 140 412).

Mixtures of certain nitromethylene derivatives with fungicidally activecompounds and their use as pesticides in crop protection are alreadyknown (U.S. Pat. No. 4,731,385; JP published specifications 63-68507,63/68505; 63/72 608; 63/72 609, 63/72 610, WO 96/03 045, Japanese patentspecification 08 245 323, Japanese patent specification 04 368 303,Japanese patent specification 05 017 311, WO 92/21 241, WO 97/22 254).Mixtures of certain open-chain nitromethylenes and nitroguanidines withfungicides are already known (Japanese published specification 30 47106; U.S. Pat. No. 5,181,587).

Mixtures of cyclopropylcarboxamides with certain nitromethylene ornitroguanidine derivatives are already known (Japanese publishedspecification 3 271 207).

Mixtures of, inter alia, imidacloprid and fungicidally active compoundsfor use in the protection of materials and against termites, but not foruse against plant-damaging pests, are already known (EP publishedspecification 0 511 541). Mixtures of imidacloprid andazolylmethylcycloalkanes, in particular triticonazole, are known from EPpublished specification 545 834.

However, hitherto it has not been known that nitroguanidine derivativesand fungicides with the exception of cyclopropylcarboxamides andtriticonazole have such a mutually beneficial effect in their activitythat they are outstandingly suitable as compositions for controllingplant pests, whilst being tolerated well by plants.

The present invention relates to compositions against plant pests whichcontain the compound of the formula (I)

in a mixture with fungicidally active compounds, except forcyclopropylcarboxamide derivatives and azolylmethylcycloalkanes.

Examples of fungicides in the compositions according to the inventionfor controlling plant pests which may be mentioned are:

-   (1) azole derivatives of the formula

-   (2) azole derivatives of the formula

-   (3) the azole derivative of the formula

-   (4) of the compound-   (5) the azole derivative of the formula

-   (6) heterocycles of the formula

-   (7) the compound of the formula

-   (8) the compound of the formula

-   (9) the compound of the formula

-   (10) the compound of the formula

-   (11) the compound of the formula

-   (12) the compound of the formula

-   (13) compounds of the formula

-   (14) compounds of the formula

-   (15) compounds of the formula

-   (16) the compound of the formula

-   (17) the compound of the formula

-   (18) the compound of the formula

-   (19) the compound of the formula

-   (20) the compound of the formula

-   (21) the compound of the formula

-   (22) the compound of the formula

-   (23) the compound of the formula

-   (24) compounds of the formula

-   (25) the compound of the formula

-   (26) the compound of the formula

-   (27) the compound of the formula

-   (28) the compound of the formula

-   (29) the compound of the formula

-   (30) the compound of the formula

-   (31) the compound of the formula

-   (32) compounds of the formula

-   (33) the compound of the formula

-   (34) the compound of the formula

-   (35) the compound of the formula

-   (36) the compound of the formula

-   (37) the compound of the formula

-   (38) compounds of the formula

-   -   in which    -   R¹⁵ and R¹⁶ independently of one another each represent        hydrogen, halogen, methyl or phenyl and    -   R¹⁷ represents hydrogen or methyl,

-   (39)    8-^(t)butyl-2-(N-ethyl-N-n-propylamino)-methyl-1,4-dioxaspiro[4.5]decane    of the formula

-   (40) the compound of the formula

-   (41) the compound of the formula

-   (42) the compound of the formula

-   (43) the compound of the formula

-   (44) benzimidazoles of the formula

-   (45) the compound of the formula

-   (46) the compound of the formula

-   (47) the compound of the formula

-   (48) the compound of the formula

-   (49) the compound of the formula

-   (50) the compound of the formula

-   (51) the compound of the formula

-   (52) the compound of the formula

-   (53) the compound of the formula

-   (54) the compound of the formula

-   (55) the compound of the formula

The active compound of the formula (1) is known from EP publishedspecification 0 375 907.

The fungicidal active compounds are also known.

Thus, for example, the following publications describe:

(1) compounds of the formula (II)

-   -   DE published specification 2 201 063    -   DE published specification 2 324 010    -   DE published specification 2 737 489    -   DE published specification 3 018 866    -   DE published specification 2 551 560    -   EP 47 594    -   DE 2 735 872        (2) the compound of the formula (III)    -   EP 68 813    -   U.S. Pat. No. 4,496,551        (3) the compound of the formula (IV)    -   DE published specification 2 429 523    -   DE published specification 2 856 974    -   U.S. Pat. No. 4,108,411        (6) compounds of the formula (VII)    -   DL 140 041        (7) the compound of the formula (VIII)    -   EP 382 375        (8) the compound of the formula (IX)    -   EP 515 901        (9) the compound of the formula (X)    -   EP 314 422        (10) the compound of the formula (XI)    -   EP 49 854        (11) the compound of the formula (XII)    -   DE published specification 1 770 288    -   U.S. Pat. No. 3,869,456        (13) compounds of the formula (XIV)    -   DE 2 207 576    -   U.S. Pat. No. 3,903,090    -   U.S. Pat. No. 3,755,350    -   U.S. Pat. No. 3,823,240        (14) compounds of the formula (XV)    -   EP 270 111        (19) the compound of the formula (XX)    -   EP 219 756        (34) the compound of the formula (XXXV)    -   U.S. Pat. No. 4,512,989        (38) compounds of the formula (XXXIX)    -   EP 398 692        (48) compound from    -   WO 97/27189        (49) compound from    -   WO 96/16048, this compound can be present in 2 tautomeric        forms (A) and (B)

Compounds from the groups (15), (16), (17), (18), (23), (34), (25),(28), (31), (32), (33) and (38) to (47) are described, for example, inK. H. Büchel, “Pflanzenschutz and Schädlingsbekämpfung”, pages 121-153,Georg Thieme-Verlag, Stuttgart, 1977.

The compound of group (39) is known from EP published specification 281842.

The compound of group (50) is known from WO 97/06 171.

The compound of group (51) is known from DE-24 33 410.

The compounds of groups (52) to (54) are known from W. Paulus,“Microbicides for the Protection of Materials”, Chapman & Hall 1993.

The compound of group (55) is known from EP-0 512 349.

In addition to the active compound of the formula (I), the activecompound combinations according to the invention contain at least onefungicidal active compound, for example selected from the compounds ofgroups (1) to (55). In addition, they may also contain other activecompounds and customary auxiliaries and additives and also diluents.

Preferred fungicidally active compounds in the compositions according tothe invention are:

kresoxim-methyl, tebuconazole, metalaxyl, azoxystrobin, triadimenol,bitertanol, fenpicolonil, cyproconazole, propiconazole, fludioxonil andtriazoxides.

The mixtures show a clear synergistic effect when the active compoundsin the active compound combinations according to the invention arepresent in certain weight ratios. However, the weight ratios of theactive compounds in the active compound combinations can be variedwithin a relatively wide range. In general,

0.1 to 10 parts by weight, preferably0.3 to 3 parts by weight of at least one fungicidal active compound, forexample from groups (1) to (55),are present per part by weight of active compound of the formula (I).

The active compound combinations according to the invention have verygood fungicidal properties. They can be employed in particular forcontrolling phytopathogenic fungi, such as Plasmodiophoromycetes,Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes,Deuteromycetes, etc.

The active compound combinations according to the invention areparticularly suitable for controlling cereal diseases, such as Erysiphe,Cochliouolus, Septoria, Pyrenophora and Leptosphaeria, and againstfungal attack on vegetables, grapevines and fruits, for example againstVenturia or Podosphaera on apples, Uncinula on grapevines orSphaerotheca on cucumbers.

The active compound combinations are also highly suitable forcontrolling animal pests, preferably arthropods, in particular insects,which are encountered in agriculture, in forestry, in the protection ofstored products and of materials, and in the hygiene sector. They areactive against normally sensitive and resistant species and against allor some stages of development. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Pediculus humanus corporis,Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Phylloxera vastatrix, Pemphigusspp., Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps,Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvatalugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. andPsylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera litura,Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp.,Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

The fact that the active compound combinations are well tolerated byplants at the concentrations required for controlling plant diseasespermits the treatment of above-ground parts of plants, of propagationstock and seeds, and of the soil.

The active compound combinations according to the invention can beconverted into the customary formulations, such as solutions, emulsions,suspensions, powders, foams, pastes, granules, aerosols,microencapsulations in polymeric compounds and in coating compositionsfor seeds, and ULV formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents include aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane, or paraffins, forexample petroleum fractions, alcohols, such as butanol or glycol andalso their ethers and esters, ketones, such as acetone, methyl ethylketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents, such as dimethylformamide and dimethyl sulphoxide, and alsowater. Liquefied gaseous extenders or carriers refer to those liquidswhich are gaseous at normal temperature and under atmospheric pressure,for example aerosol propellants, such as halogenated hydrocarbons, andalso butane, propane, nitrogen and carbon monoxide. Suitable solidcarriers are: for example ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates. Suitable solid carriers for granules are: forexample crushed and fractionated natural rocks, such as calcite, marble,pumice, sepiolite and dolomite, or else synthetic granules of inorganicand organic meals, and granules of organic materials such as sawdust,coconut shells, maize cobs and tobacco stalks. Suitable emulsifiersand/or foam formers are: for example nonionic and anionic emulsifiers,such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, or else protein hydrolysates. Suitabledispersants are: for example lignin-sulphite waste liquors andmethylcellulose.

Tackifiers, such as carboxymethylcellulose and natural and syntheticpolymers, in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids, such as cephalins and lecithins and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients, such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

In the formulations, the active compound combinations according to theinvention can be present as a mixture with other known active compounds,such as fungicides, insecticides, acaricides and herbicides, and asmixtures with fertilizers or plant growth regulators.

The active compound combinations can be employed as such, in the form oftheir formulations or of the use forms prepared therefrom, such asready-to-use solutions, emulsifiable concentrates, emulsions,suspensions, wettable powders, soluble powders and granules.

The application is carried out in a customary manner, for example bywatering, spraying, atomizing, scattering, spreading, dry dressing, wetdressing, liquid dressing, slurry treatment of seeds or incrustation.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a relatively wide range. Ingeneral, they are between 1 and 0.0001% by weight, preferably between0.5 and 0.001%.

In the treatment of seed, the amounts of active compound which aregenerally required are from 0.001 to 50 g per kilogram of seed,preferably from 0.01 to 10 g. In the treatment of the soil, activecompound concentrations of from 0.00001 to 0.1% by weight, preferablyfrom 0.0001 to 0.02% by weight, are required at the site of action.

Furthermore, it has been found that the active compound combinationsaccording to the invention have a potent insecticidal action againstinsects which destroy industrial materials.

The following insects may be mentioned by way of example and as beingpreferred, but without any limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

Dermapterans, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as Lepisma saccharina.

Industrial materials are to be understood as meaning, in the presentcontext, non-live materials such as, preferably, plastics, glues, sizes,paper and board, leather, wood and timber products, and coatings.

The materials to be protected against attack by insects are veryparticularly wood and timber products.

Wood and timber products which can be protected by the compositionaccording to the invention or mixtures comprising such a composition areto be understood as meaning, for example, construction timber, woodenbeams, railway sleepers, bridge components, jetties, wooden vehicles,boxes, pallets, containers, telephone poles, wood panelling, windows anddoors made of wood, plywood, particle board, joiner's articles, or woodproducts which, quite generally, are used in the construction of housesor in joinery.

The active compound combinations can be used as such, in the form ofconcentrates or generally customary formulations, such as powders,granules, solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersant and/or binder or fixative, waterrepellent, if appropriate desiccants and UV stabilizers and, ifappropriate, dyes and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for the protection ofwood and wooden materials comprise the active compound according to theinvention at a concentration of 0.0001 to 95% by weight, in particular0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thespecies and the occurrence of the insects and on the medium. The optimumrate of application can be determined upon use in each case by testseries. However, in general, it suffices to employ 0.0001 to 20% byweight, preferably 0.001 to 10% by weight, of the active compound, basedon the material to be protected.

The solvent and/or diluent used is an organochemical solvent or solventmixture and/or an oily or oil-type organochemical solvent or solventmixture of low volatility and/or a polar organochemical solvent orsolvent mixture and/or water and, if appropriate, an emulsifier and/orwetting agent.

Organochemical solvents which are preferably employed are oily oroil-type solvents having an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C. Substances which are usedas such oily and oil-type solvents which have low volatility and areinsoluble in water are suitable mineral oils or their aromaticfractions, or mineral-oil-containing solvent mixtures, preferably whitespirit, petroleum and/or alkylbenzene.

Substances which are advantageously used are mineral oils with a boilingrange of 170 to 220° C., white spirit with a boiling range of 170 to220° C., spindle oil with a boiling range of 250 to 350° C., petroleumor aromatics of the boiling range 160 to 280° C., essence of turpentineand the like.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boilingrange of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-type solvents of low volatility having anevaporation number of above 35 and a flash point of above 30° C.,preferably above 45° C., can be partially replaced by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flash point ofabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

In a preferred embodiment, part of the organochemical solvent or solventmixture is replaced by an aliphatic polar organochemical solvent orsolvent mixture. Substances which are preferably used are aliphaticorganochemical solvents having hydroxyl and/or ester and/or ethergroups, such as, for example, glycol ethers, esters or the like.

The organochemical binders used within the scope of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se and can be diluted with water and/or are soluble ordispersible or emulsifiable in the organochemical solvents employed, inparticular binders composed of, or comprising, an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenolic resin, hydrocarbon resin, such asindene-coumarone resin, silicone resin, drying vegetable oils and/ordrying oils and/or physically drying binders based on a natural and/orsynthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Up to 10% by weight of bitumen orbituminous substances can also be used as binders. In addition, dyes,pigments, water repellents, odour-masking substances and inhibitors oranticorrosives known per se and the like can also be employed.

The composition or the concentrate preferably comprises, in accordancewith the invention, at least one alkyd resin or modified alkyd resinand/or a drying vegetable oil as the organochemical binders. Preferablyused according to the invention are alkyd resins with an oil content ofover 45% by weight, preferably 50 to 68% by weight.

All or some of the abovementioned binder can be replaced by a fixative(mixture) or a plasticizer (mixture). These additives are intended toprevent volatilization of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters,such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate,the phosphoric esters, such as tributyl phosphate, the adipic esters,such as di-(2-ethylhexyl) adipate, the stearates, such as butyl stearateor amyl stearate, the oleates, such as butyl oleate, the glycerol ethersor relatively high-molecular-weight glycol ethers, glycerol esters andp-toluene-sulphonic esters.

Fixatives are chemically based on polyvinyl alkyl ethers, such as, forexample, polyvinyl methyl ether, or ketones, such as benzophenone orethylenebenzophenone.

Also particularly suitable as a solvent or diluent is water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective protection of wood is achieved by large-scaleindustrial impregnation processes, for example vacuum, double-vacuum orpressure processes.

If appropriate, the ready-to-use compositions can additionally compriseother insecticides.

Suitable additional components which may be admixed are, preferably, theinsecticides mentioned in WO 94/29 268. The compounds mentioned in thatdocument are expressly incorporated into the present application byreference.

Very particularly preferred components which may be admixed areinsecticides, such as chlorpyriphos, phoxim, silafluofen, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron.

The good pesticidal activity of the active compound combinationsaccording to the invention is demonstrated by the examples below.Whereas the individual active compounds or the known active compoundcombinations have weaknesses in the pesticidal activity, the tables ofthe examples below show unambiguously that the activity which was foundof the active compound combinations according to the invention isgreater than the sum of the activities of the individual activecompounds and also greater than the activities of the known activecompound combinations.

In the examples below, the active compound of the formula (I)

is used.

The fungicidally active compounds which are also used are given in theexamples.

EXAMPLE A Phaedon Larvae Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof an active compound or an active compound combination is mixed withthe stated amounts of solvent and emulsifier, and the concentrate isdiluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example, the following active compound combinationsaccording to the present invention show a synergistically increasedactivity compared to the individually applied active compounds:

TABLE A (plant-damaging insects) Phaedon larvae test Activecompound/active com- Active compound/active com- pound mixture poundmixture concentration in % Kill in %

0.00016  0.000032 20  0

0.1     0 formula (I) + kresoxim-methyl 0.00016 + 0.1 75

EXAMPLE B Plutella Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof an active compound or an active compound combination is mixed withthe stated amounts of solvent and emulsifier, and the concentrate isdiluted with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the diamondback moth (Plutellaxylostella) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following active compound combinationsaccording to the present invention show a synergistically increasedactivity compared to the individually applied active compounds:

TABLE B (plant-damaging insects) Plutella test Active com- pound/activecompound Kill Active compound/active compound mixture concen- in mixturetration in % %

0.0008  0

0.02  0

0.1  0 formula (I) + tebuconazole 0.0008 + 0.02 100 fomula (II) +metalaxyl 0.0008 + 0.1  100

EXAMPLE C

Heliothis virescens Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof an active compound or an active compound combination is mixed withthe stated amounts of solvent and emulsifier, and the concentrate isdiluted with water to the desired concentration.

Soya bean shoots (Glycine max) are treated by being dipped into theactive compound preparation of the desired concentration and arepopulated with Heliothis virescens caterpillars while the leaves arestill moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following active compound combinationsaccording to the present invention show a synergistically enhancedactivity in comparison to the individually applied active compounds:

TABLE C (plant-damaging insects) Heliothis virescens test Active com-pound/active compound Kill Active compound/active compound mixtureconcen- in mixture tration in % %

0.00016  50

0.0008  0 formula (I) + azoxystrobin 0.00016 + 0.0008 100

EXAMPLE D Nephotettix Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof an active compound or an active compound combination is mixed withthe stated amounts of solvent and emulsifier, and the concentrate isdiluted with water to the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into theactive compound preparation of the desired concentration and arepopulated with the green rice leaf hopper (Nephotettix cincticeps) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all the leaf hoppers have been killed; 0% means that none ofthe leaf hoppers have been killed.

In this test, for example, the following active compound combinationsaccording to the present invention show a synergistically enhancedactivity in comparison to the individually applied active compounds:

TABLE D (plant-damaging insects) Nephotettix test Active com-pound/active compound Kill Active compound/active compound mixtureconcen- in mixture tration in % %

0.00000128 0

0.1 0 formula (I) + metalaxyl 0.00000128 + 0.1 85

EXAMPLE E Critical Concentration Test/Soil Insects

Test insect: Spodoptera frugiperda

Solvent: 4 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof the active compound or the active compound mixture is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

The active compound preparation is mixed intimately with soil. Here, theconcentration of the active compound in the preparation is almostirrelevant; only the amount by weight of active compound or activecompound mixture per volume unit of soil, which is stated in ppm (mg/1),matters.

Soil is filled into 0.5 l pots and these are allowed to stand at 20° C.Immediately after preparation, 3 pre-germinated maize corns are placedinto each pot. After the maize corns have emerged, boring sleeves areplaced onto the pots. 9 days after preparation, the maize is populatedwith the test insects. After a further 5 days, the kill in % isdetermined. 100% means that all test insects have been killed; 0% meansthat the number of insects which are still alive is the same as for theuntreated control.

In this test, for example, the following active compound combinationsaccording to the present invention show a synergistically enhancedactivity compared to the individually applied active compounds:

TABLE E (plant-damaging insects) Spodoptera frugiperda test Active com-pound/active compound Kill Active compound/active compound mixtureconcen- in mixture tration in ppm %

 1.25  0.60  0.30 100  98  50

20.00  0

20.00  0

20.00  0

20.00  0

20.00  0

20.00  0

20.00  0

20.00  0 formula (I) + tebuconazole 1.25 + 20.00 100 0.60 + 20.00  800.30 + 20.00  80 formula (I) + triadimenol 1.25 + 20.00 100 0.60 + 20.00 80 0.30 + 20.00  50 formula (I) + bitertanol 1.25 + 20.00 100 0.60 +20.00  80 0.30 + 20.00  80 formula (I) + fenpiclonil 1.25 + 20.00 1000.60 + 20.00  90 0.30 + 20.00  80 formula (I) + azoxystrobin 1.25 +20.00 100 0.60 + 20.00  80 0.30 + 20.00  0 formula (I) + metalaxyl1.25 + 20.00 100 0.60 + 20.00  95 0.30 + 20.00  0 formula (I) +cyproconazol 1.25 + 20.00 100 0.60 + 20.00  50 0.30 + 20.00  0 formula(I) + propiconazole 1.25 + 20.00 100 0.60 + 20.00  90 0.30 + 20.00  70

EXAMPLE F Critical Concentration Test/Root-Systemic Action

Test insect: Phaedon cochleariae larvae

Solvent: 4 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof the active compound or the active compound mixture is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

The active compound preparation is mixed intimately with soil. Here, theconcentration of the active compound in the preparation is almostirrelevant; only the amount by weight of active compound or activecompound mixture per volume unit of soil, which is stated in ppm (mg/l),matters.

Soil is filled into 250 ml pots and these are planted with cabbage(Brassica oleracea). The active compound or the active compoundcombination can thus be taken up by the plant roots from the soil andtransported into the leaves.

After 7 days, the leaves are populated with the abovementioned testanimals. After a further 3 days, the kill in % is determined. 100% meansthat all test insects have been killed; 0% means that the number ofinsects which are still alive is the same as in the untreated control.

In this test, for example, the following active compound combinationsaccording to the present invention show a synergistically enhancedactivity compared to the individually applied active compounds:

TABLE F (plant-damaging insects) Phaedon cochleariae test Active com-pound/active compound Kill Active compound/active compound mixtureconcen- in mixture tration in ppm %

 1.25  0.60  0.30 100  80  50

20.00  0

20.00  0

20.00  0

20.00  0

20.00  0

20.00  0

20.00  0 formula (I) + tebuconazole 1.25 + 20.00 100 0.60 + 20.00  800.30 + 20.00  80 formula (I) + triadimenol 1.25 + 20.00 100 0.60 + 20.00100 0.30 + 20.00 100 formula (I) + bitertanol 1.25 + 20.00 100 0.60 +20.00 100 0.30 + 20.00  70 formula (I) + fenpiclonil 1.25 + 20.00 1000.60 + 20.00 100 0.30 + 20.00  70 formula (I) + azoxystrobin 1.25 +20.00 100 0.60 + 20.00  90 0.30 + 20.00  50 formula (I) + metalaxyl1.25 + 20.00 100 0.60 + 20.00 100 0.30 + 20.00  50 formula (I) +propiconazole 1.25 + 20.00 100 0.60 + 20.00 100 0.30 + 20.00  90

EXAMPLE G

Formula for the calculation of the efficacy of a combination of twoactive compounds

The expected activity for a given combination of two active compoundscan be calculated as follows (cf. Colby, S. R., “Calculating Synergisticand Antagonistic Responses of Herbicide Combinations”, Weeds 15, pages20-22, 1967):

if

-   X is the efficacy, expressed in % of the untreated control, when    applying the active compound A at an application rate of m g/ha,-   Y is the efficacy, expressed in % of the untreated control, when    applying the active compound B at an application rate of n g/ha,-   E is the efficacy, expressed in % of the untreated control, when    applying the active compounds A and B at application rates of m and    n g/ha,    then

$E = {X + Y - {\frac{X \times Y}{100}.}}$

If the actual fungicidal activity exceeds the calculated value, then theactivity of the combination is superadditive, i.e. a synergistic effectexists. In this case, the efficacy which was actually observed must begreater than the value for the expected efficacy (E) calculated from theformula set out above.

Phytophthora Test (Tomato)/Protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof the active compound or the active compound mixture is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with thecommercial active compound preparation at the stated application rate.After the spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Phytophthora infestans. The plants are thenplaced in an incubation cabin at approximately 20° C. and 100% relativeatmospheric humidity.

Evaluation is carried out 3 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

The table below shows unambiguously that the activity which was found ofthe active compound combinations according to the invention is greaterthan the calculated efficacy (see above), i.e., a synergistic effect ispresent.

TABLE G Phytophthora test (tomato)/protective Effi- Active com- cacypound/active in % Active compound/active compound mix- calcula- compoundmixture ture in g/ha ted/found

500 51

500  5 formula (I) + propiconazole 500 + 500 53/69

500 55

500  0 formula (I) + triadimenol 500 + 500 55/63

 50 19

 50 42 formula (I) + metalaxyl 50 + 50 53/68

EXAMPLE H Sphaerotheca Test (Cucumber)/Protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof the active compound or the active compound mixture is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with thecommercial active compound preparation at the stated application rate.After the spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Sphaerotheca fuliginea. The plants are thenplaced in an incubation cabin at approximately 20° C. and 100% relativeatmospheric humidity.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

The table below shows unambiguously that the activity which was found ofthe active compound combinations according to the invention is greaterthan the calculated efficacy (see above), i.e., a synergistic effect ispresent.

TABLE H Sphaerotheca test (cucumber)/protective Effi- Active com- cacypound/active in % Active compound/active compound mix- calcula- compoundmixture ture in g/ha ted/found

 10  0

 10 70 formula (I) + cyproconazole 10 + 10 70/80

500  0

500 50 formula (I) + fenpiclonil 500 + 500 50/83

EXAMPLE I Botrytis Test (Bean)/Protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof the active compound or the active compound mixture is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with theactive compound preparation at the stated application rate. After thespray coating has dried on, 2 small pieces of agar colonized by Botrytiscinerea are placed onto each leaf. The inoculated plants are placed in adark chamber at approximately 20° C. and 100% relative atmospherichumidity.

2 days after the inoculation, the size of the disease spots on theleaves is evaluated. 0% means an efficacy which corresponds to that ofthe control, whereas an efficacy of 100% means that no infection isobserved.

The table below shows unambiguously that the activity which was found ofthe active compound combinations according to the invention is greaterthan the calculated efficacy (see above), i.e., a synergistic effect ispresent.

TABLE I Botrytris test (bean)/protective Effi- Active com- cacypound/active in % Active compound/active compound mix- calcula- compoundmixture ture in g/ha ted/found

 10  0

 10 40 formula (I) + fludioxonil 10 + 10 40/83

100  4

100 80 formula (I) + tebuconazole 100 + 100 81/94

EXAMPLE J

Fusarium culmorum Test (Wheat)/Seed Treatment

The active compounds are applied as a dry dressing. They are prepared byextending the active compound in question with ground minerals to give afinely pulverulent mixture which ensures even distribution on thesurface of the seeds.

For the dressing, the infected seeds are shaken with the dressing in aclosed glass bottle for 3 minutes.

2×100 seeds of the wheat are sown at a depth of 1 cm into standard soil,and the wheat is cultivated in a greenhouse at a temperature ofapproximately 18° C. and at a relative atmospheric humidity ofapproximately 95% in seed containers receiving 15 hours of light perday.

The evaluation of the plants for symptoms is carried out approximately 3weeks after sowding. 0% means an efficacy which corresponds to that ofthe control, whereas an efficacy of 100% means that no infection isobserved.

TABLE J Fusarium culmorum test (wheat)/seed treatment Active com- Effi-pound/active cacy Active compound/active compound in compound mixturemixture in g/ha %

75 0

75 0

75 13.5 formula (I) + fludioxonil 37.5 + 37.5 38.5 formula (I) +triadimenol 37.5 + 37.5 30.5

EXAMPLE K Puccinia Test (Wheat)/Protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with theactive compound preparation at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature ofapproximately 20° C. and a relative atmospheric humidity of 80% topromote the development of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE K Puccinia (wheat)/protective Active com- Effi- pound/active cacyActive compound/active compound in compound mixture mixture in g/ha %

18.75  0

18.75 13 formula (I) + triadimenol 9.375 + 9.375 63

EXAMPLE L

Pyrenophora teres Test (Barley)/Protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with theactive compound preparation at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Pyrenophora teres. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature ofapproximately 20° C. and a relative atmospheric humidity ofapproximately 80%.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE L Pyrenophora teres test (barley)/protective Effi- Active com-cacy pound/active in % Active compound/active compound calcula- compoundmixture mixture in g/ha ted/found

62.5  18.75  0 20

62.5  40

18.75  0 formula (I) + azoxystrobin 9.375 + 9.375 60 formula (I) +triazoxides 31.25 + 31.25 70

EXAMPLE M Erysiphe Test (Barley)/Protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound-combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate:

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80% topromote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE M Erysiphe test (barley)/protective Effi- Active com- cacypound/active in % Active compound/active compound calcula- compoundmixture mixture in g/ha ted/found

62.5  0

62.5  0 formula (I) + kresoxim-methyl 31.25 + 31.25 75

EXAMPLE N Critical Concentration Test/Root Systemic Action

Test insect: Spodoptera frugiperda

Solvent: 4 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The preparation of active compound is mixed intimately with soil. Here,the concentration of the active compound in the preparation is virtuallyimmaterial; only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/1), matters. The soil is filled into250 ml pots and these are allowed to stand at 20° C.

Immediately after preparation, 3 maize corns are placed into each pot.14 days after the preparation, the test insects are placed into aninsect bracket and attached to the plant. 4 days after the infection,the efficacy of the active compound is determined in % by counting thedead and live test insects. The efficacy is 100% if all test insectshave been killed; it is 0% if the same number of test insects is aliveas in the untreated control.

TABLE N Spodoptera frugiperda test Kill in % at active compound/activeActive compound/active compound mixture compound mixture concentrationin ppm

0.15 ppm = 50%

5.00 ppm = 0% compound according to formula (I) + 0.15 ppm + 5.00 ppm =80% compound of group (49)

EXAMPLE O Critical Concentration Test/Soil Insects

Test insect: Diabrotica balteata—larvae in the soil

Solvent: 4 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration. Here, the concentration of theactive compound in the preparation is almost irrelevant; only the amountby weight of active compound per volume unit of soil, which is stated inppm (mg/1), matters. The soil is filled into 0.5 l pots and these areallowed to stand at 20° C.

Immediately after preparation, 5 maize corns are placed into each pot.After 3 days, the test insects are placed into the treated soil. After afurther 7 days, the efficacy is determined. The efficacy is calculatedfrom the number of maize plants which have emerged.

Active compounds, application rates and results are shown in the tablebelow:

TABLE O Soil insecticides Diabrotica balteata-larvae in the soil Kill in% at active Active compound compound concen- (constitution) trations inppm

 0.15 ppm = 0%

20.00 ppm = 70% formula (I) + compound according to 0.15 ppm + 20.00(50) ppm = 70%

TABLE P Soil insecticides Diabrotica balteata-larvae in the soil Kill in% at active Active compound compound concen- (constitution) trations inppm

 0.30 ppm = 50%

20.00 ppm = 0% formula (I) + compound according to 0.15 ppm + 20.00 (48)ppm = 90%

1. A composition comprising the compound of the general formula (I)

and metalaxyl.
 2. The composition according to claim 1, wherein thecomposition comprises from 0.1 to 10 parts by weight of metalaxyl perpart by weight of active compound of the formula (I).
 3. A process forcontrolling fungi or insects, characterized in that active compoundcombinations according to claim 1 are allowed to act on the fungi,insects and/or their habitat.
 4. (canceled)
 5. A process for preparing acomposition according to claim 1, comprising mixing the compositionaccording to claim 1 with extenders and/or surfactants.